Sodium Carbonate → 7-Fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

HRID 2223088ノート

反応式

HRID 2223088 の反応式
Cl[C:2]1[C:8]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=2[N:6]([CH3:14])[C:5](=[O:15])[CH2:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>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:13][C:10]1[CH:11]=[CH:12][C:7]2[N:6]([CH3:14])[C:5](=[O:15])[CH2:4][N:3]=[C:2]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:8]=2[CH:9]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 597138735-Chloro-7-fluoro-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

生成物 1

HCID 443661797-Fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one収率 76%

試薬・触媒・溶媒 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒

実験手順

As illustrated in the scheme above and following General Procedure 4, 5-chloro-7-fluoro-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (0.201 g, 0.887 mmol), Na2CO3 (0.0940 g, 0.887 mmol), PdCl2(dppf) (0.0362. g, 0.0443 mmol) and phenylboronic acid (0.108 g, 0.886 mmol) were combined and heated for 13 h. After workup, purification of the crude product by silica gel column chromatography (3:1 CH2Cl2:EtOAc) provided the title compound (0.180 g, 76%). 1H-NMR (CDCl3): δ 7.64-7.60 (m, 2H), 7.51-7.45 (m, 1H), 7.44-7.39 (m, 2H), 7.34 (dd, J=4.8 Hz, J=9.2 Hz, 1H), 7.31-7.25 (m, 1H), 7.02 (dd, J=2.8 Hz, J=8.8 Hz, 1H), 4.84 (d, J=10.8 Hz, 1H), 3.78 (d, J=10.8 Hz, 1H), 3.40 (s, 3H). MS (ESI) (M+H)+=269.

後処理

  1. temperatureheated for 13 h
  2. customAfter workup, purification of the crude product by silica gel column chromatography (3:1 CH2Cl2:EtOAc)

出典と根拠

ORDレコード
ord-94315c751e8b4bf9b15ab6a8f5b6c851
出典データセット
uspto-grants-2008_05
特許番号
US07375101B2

反応ノート

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