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Potassium Carbonate → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-morpholinopyridin-4-yl)benzo[d]thiazol-6-yl)acetate

HRID 879428
ノート
印刷プレビュー

反応式

HRID 879428 の反応式
[C:1]([O:5][C@@H:6]([C:12]1[C:33]([CH3:34])=[CH:32][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:30][CH2:29]N(C)[CH2:27][CH2:26]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1OS(C(F)(F)F)(=O)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[Cl:43][C:44]1[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=1.C(=O)([O-])[O-:54].[K+].[K+]>CC(OC)(C)C.COC1C=CC=C(OC)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1.C1C=[C-]C(CCN)=CC=1.Cl[Pd+].C(COC)OC.C(OCC)(=O)C>[C:1]([O:5][C@@H:6]([C:12]1[C:33]([CH3:34])=[CH:32][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:26][CH2:27][O:54][CH2:29][CH2:30]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:47]1[CH:48]=[CH:49][C:44]([Cl:43])=[CH:45][CH:46]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:2])[CH3:3]
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 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acid2 回HCID 131732631(S)-ethyl 2-tert-butoxy-2-(5-methyl-2-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate

生成物 1

HCID 86700235(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-morpholinopyridin-4-yl)benzo[d]thiazol-6-yl)acetate

試薬・触媒・溶媒 3

HCID 71311105
SPhos Palladacycle
触媒
2 回
HCID 80711,2-Dimethoxyethane溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A mixture of (S)-ethyl 2-tert-butoxy-2-(5-methyl-2-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate (20 mg, 0.0324 mmol), 4-chlorophenyboronic acid (10 mg, 0.063 mmol), SPhos precatalyst (3.3 mg, 0.0049 mmol) and powdered potassium carbonate (18 mg, 0.129 mmol) in anhydrous dimethoxyethane (0.75 mL) was sparged with nitrogen for 5 minutes, then heated in microwave at 120° C. for 1.5 h. Added more 4-chlorophenyboronic acid and SPhos precatalyst (3.3 mg, 0.0049 mmol) and continued reaction. Reaction mixture was diluted with ethyl acetate, washed with brine, dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 40% EtOAc/Hex) to give product. LCMS-ESI+: calc'd for C31H35ClN3O4S: 580.2 (M+H+); Found: 580.3 (M+H+).

後処理

  1. customwas sparged with nitrogen for 5 minutes
  2. customreaction
  3. customReaction mixture
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by CombiFlash (0 to 40% EtOAc/Hex)
  9. customto give product

出典と根拠

ORDレコード
ord-a5f6f03f816147c7bdc907438768fd53
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987250B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート