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Methanol → Methyl 6-(4-{1,2-dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)pyridazine-3-carboxylate

HRID 1644874
ノート
印刷プレビュー

反応式

HRID 1644874 の反応式
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:32])([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[CH:20][N:19]=3)[CH:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.CN([CH:36]=[O:37])C.[CH3:38][OH:39]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:32][C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[N:4]=[N:3][C:2]([C:38]([O:37][CH3:36])=[O:39])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:20][N:19]=1)[CH:15]([CH3:17])[CH3:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 887MethanolHCID 6228DimethylformamideHCID 57910808HCID 57910808、化合物

生成物 1

HCID 57910811Methyl 6-(4-{1,2-dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)pyridazine-3-carboxylate

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
触媒
HCID 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

Palladium (II) acetate (8.00 mg, 0.0350 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (39.0 mg, 0.070 mmol) were added successively to a stirred solution of 5b (155 mg, 0.349 mmol) in triethylamine:DMF:MeOH (4.00 mL of a 1:10:10 mixture, respectively) at rt. A gentle stream of the carbon monoxide gas was bubbled through the reaction mixture for approximately 15 min, after which the resulting mixture was heated to 70° C. under a carbon monoxide atmosphere (balloon) for about 5 h. After cooling to rt, the reaction mixture was filtered through a short column of CELITE®, eluting with DCM. The filtrate was partially concentrated in vacuo and diluted with EtOAc. The organic phase was washed with water, brine, dried (sodium sulfate) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 30%-100% EtOAc/hexanes as eluent) afforded the title compound 5c. m/z (ES) 469 (MH)+. 1HNMR (500 MHz, CDCl3): δ 8.62 (d, 1H, J=4.8 Hz), 8.41 (m, 1H), 8.22 (d, 1H, J=8.7 Hz), 8.08 (d, 2H, J=8.8 Hz), 7.96 (d, 1H, J=8.9 Hz), 7.75 (dt, 1H, J=1.7, 7.7 Hz), 7.56 (d, 2H, J=8.7 Hz), 7.53 (d, 1H, J=7.8 Hz), 7.26 (dd, 1H, J=5.2, 7.3 Hz), 7.19 (m, 2H), 5.23 (s, 2H), 4.10 (s, 3H), 3.11 (m, 1H, 6.6 Hz), 1.73 (s, 3H), 0.89 (d, 3H, J=6.7 Hz), 0.83 (d, 3H, J=6.8 Hz).

後処理

  1. customat rt
  2. customA gentle stream of the carbon monoxide gas was bubbled through the reaction mixture for approximately 15 min
  3. temperatureAfter cooling to rt
  4. filtrationthe reaction mixture was filtered through a short column of CELITE®
  5. washeluting with DCM
  6. concentrationThe filtrate was partially concentrated in vacuo
  7. additiondiluted with EtOAc
  8. washThe organic phase was washed with water, brine
  9. dry with materialdried (sodium sulfate)
  10. concentrationconcentrated in vacuo
  11. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 30%-100% EtOAc/hexanes as eluent)

出典と根拠

ORDレコード
ord-3edd65837f4d4152aa4158b6575f53fd
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08124628B2

反応ノート

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