Dimethylformamide → 10-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575184ノート

反応式

HRID 575184 の反応式
[Br:1][C:2]1[C:3]([F:17])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13](I)[N:14]=[C:7]3[C:6]=2[CH:16]=1.C[Si](N[Si](C)(C)C)(C)C.C[N:28](C)[CH:29]=[O:30]>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].C(Cl)Cl>[Br:1][C:2]1[C:3]([F:17])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13]([C:29]([NH2:28])=[O:30])[N:14]=[C:7]3[C:6]=2[CH:16]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 13838HexamethyldisilazaneHCID 6831272510-Bromo-9-fluoro-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

生成物 1

HCID 8669305110-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide収率 55%

試薬・触媒・溶媒 1

HCID 178418807HCID 178418807、化合物触媒

反応条件

温度
70 °C

実験手順

Similar to as described in Example 10, A suspension of 10-bromo-9-fluoro-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (16.0 g, 39.12 mmol, 1.00 equiv)(US2012/245144A1), HMDS (19.3 g, 119.88 mmol, 3.06 equiv) and Pd(dppf)Cl2 CH2Cl2 (1.6 g, 1.95 mmol, 0.05 equiv) in N,N-dimethylformamide (240 mL) was stirred for 2 h at 70° C. under a carbon monoxide atmosphere (1 atm). After cooling to room temperature the reaction was quenched by addition of methanol (5 mL), diluted by ethyl acetate (1 L), washed with water (200×4 mL) and brine (200 mL), dried over sodium sulfate, and concentrated under vacuum. The residue was further purified by FC(Silica and ethyl acetate/petroether 2:1) to give 7.0 g (55%) of the titled compound as a grey solid.

後処理

  1. temperatureAfter cooling to room temperature the reaction
  2. customwas quenched by addition of methanol (5 mL)
  3. additiondiluted by ethyl acetate (1 L)
  4. washwashed with water (200×4 mL) and brine (200 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was further purified by FC(Silica and ethyl acetate/petroether 2:1)

出典と根拠

ORDレコード
ord-2b646a4c911543769d8ce93216730eed
出典データセット
uspto-grants-2015_05
特許番号
US09034866B2

反応ノート

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