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Ethyl Acetate → 8-Cyclopropanesulfonyl-4,5-difluoro-6-(2-fluoro-4-iodo-phenyl)-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one

HRID 1914881
ノート
印刷プレビュー

反応式

HRID 1914881 の反応式
[F:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[C:5]2[NH:11][C:12](=[O:22])[N:13]([C:14]3[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=3[F:21])[C:4]=2[C:3]=1[F:23].[CH:24]1([S:27](Cl)(=[O:29])=[O:28])[CH2:26][CH2:25]1.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCCCCC>[CH:24]1([S:27]([N:11]2[C:5]3[C:6]4[O:10][CH:9]=[N:8][C:7]=4[C:2]([F:1])=[C:3]([F:23])[C:4]=3[N:13]([C:14]3[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=3[F:21])[C:12]2=[O:22])(=[O:29])=[O:28])[CH2:26][CH2:25]1
参加物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 8857Ethyl AcetateHCID 2760919Cyclopropanesulfonyl chlorideHCID 67253227HCID 67253227、化合物

生成物 1

HCID 672370348-Cyclopropanesulfonyl-4,5-difluoro-6-(2-fluoro-4-iodo-phenyl)-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one収率 68.2%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344
Dichloromethane
溶媒
HCID 8058Hexane溶媒

実験手順

TEA (78 mg, 0.55 mmol) and DMAP (10 mg) were added to a solution of 4,5-difluoro-6-(2-fluoro-4-iodo-phenyl)-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-15a: 80 mg, 0.178 mmol) in dry DCM (5 mL) at 0° C. and the resulting mixture was stirred for 15 minutes. This was followed by the addition of cyclopropanesulfonyl chloride (39 mg, 0.27 mmol) and stirring was continued for a further 3 hours at room temperature. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was partitioned between water (50 mL) and ethyl acetate (50 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (20-30% ethyl acetate in hexane) afforded 65 mg of the product (65% yield). H1NMR (CDCl3, 300 MHz): δ 8.14 (s, 1H), 7.72-7.65 (m, 2H), 7.28-7.24 (m, 1H), 3.35-3.25 (m, 1H), 1.75-1.60 (m, 2H), 1.35-1.25 (m, 2H).

後処理

  1. stirringstirring
  2. waitwas continued for a further 3 hours at room temperature
  3. customThe reaction mixture was partitioned between water (50 mL) and ethyl acetate (50 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (20-30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-b03a0644f90148ca87195563ccd27d66
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08614239B2

反応ノート

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