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Dichloromethane → 5-[2,3-Difluoro-2'-(methylsulfonyl)biphenyl-4-yl]pyrazin-2-amine

HRID 1523965
ノート
印刷プレビュー

反応式

HRID 1523965 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[C:4]([F:15])[C:3]=1[F:16].[CH3:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O)(=[O:20])=[O:19].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:16][C:3]1[C:4]([F:15])=[C:5]([C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH:6]=[CH:7][C:2]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[S:18]([CH3:17])(=[O:20])=[O:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27735392-(Methylsulfonyl)phenylboronic AcidHCID 903145395-(4-Bromo-2,3-difluorophenyl)pyrazin-2-amine

生成物 1

HCID 903143235-[2,3-Difluoro-2'-(methylsulfonyl)biphenyl-4-yl]pyrazin-2-amine収率 41%

試薬・触媒・溶媒 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒

実験手順

Nitrogen sparged DMSO (0.73 ml) was added to a mixture of 5-(4-bromo-2,3-difluorophenyl)pyrazin-2-amine (50 mg, 0.18 mmol), (2-(methylsulfonyl)phenyl)boronic acid (35 mg, 0.18 mmol), K2CO3 (73 mg, 0.532 mmol) and PdCl2(dppf).CH2Cl2 (13 mg, 0.018 mmol) and heated at 80° Celsius for 2.5 hours. The mixture was cooled to rt and partitioned between sat. NaHCO3 and EtOAc. The organic layer was isolated, dried over MgSO4, and concentrated to dryness. Purification by FCC afforded the title compound (26 mg, 41%). MS (ESI): mass calcd. for C17H13F2N3O2S, 361.07; m/z found, 362.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.44-8.41 (m, 1H), 8.14 (dd, J=7.9, 1.4, 1H), 8.04 (d, J=1.5, 1H), 7.84 (m, 1H), 7.78 (m, 1H), 7.75-7.66 (m, 1H), 7.53 (dd, J=7.5, 1.3, 1H), 7.30 (dd, J=11.6, 4.9, 1H), 6.85 (s, 2H), 3.06 (s, 3H).

後処理

  1. customNitrogen sparged DMSO (0.73 ml)
  2. custompartitioned between sat. NaHCO3 and EtOAc
  3. customThe organic layer was isolated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. customPurification by FCC

出典と根拠

ORDレコード
ord-ed3a668adfd948819e11d59cb8833af6
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09079866B2

反応ノート

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