Sodium triacetoxyborohydride → 5-bromo-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-2-nitroaniline

HRID 1848094ノート

反応式

HRID 1848094 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH3:26][S:27][C:28]1[S:29][C:30]2[CH:36]=[C:35]([CH:37]=O)[CH:34]=[CH:33][C:31]=2[N:32]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH:7][CH2:37][C:35]1[CH:34]=[CH:33][C:31]2[N:32]=[C:28]([S:27][CH3:26])[S:29][C:30]=2[CH:36]=1

参加物

6

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 53147665-Bromo-2-nitroanilineHCID 547753816-Benzothiazolecarboxaldehyde, 2-(methylthio)-

生成物 1

HCID 866810725-bromo-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-2-nitroaniline収率 73%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

To a stirred mixture of 5-bromo-2-nitroaniline (714 mg, 4.0 mmol) in TFA (7 mL) at −15° C. under argon, was added NaBH(OAc)3 (1.2 g, 5.4 mmol) in small portions. The mixture was stirred for 15 min, then a solution of 2-(methylthio)benzo[d]thiazole-6-carbaldehyde in CH2Cl2 (2 mL) was added dropwise. The mixture was stirred for 30 min then concentrated under reduced pressure to give a red oil. The oil was partitioned between EtOAc (200 mL) and saturated aq NaHCO3 (100 mL). The organic layer was separated and washed with brine (100 mL). The organic layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with a gradient of 100% hexanes to 50% hexanes in EtOAc to afford 5-bromo-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-2-nitroaniline (1.1 g, 73%) as a yellow solid. LCMS (ESI) m/z 409, 411 (M+H)+.

後処理

  1. stirringThe mixture was stirred for 30 min
  2. concentrationthen concentrated under reduced pressure
  3. customto give a red oil
  4. customThe oil was partitioned between EtOAc (200 mL) and saturated aq NaHCO3 (100 mL)
  5. customThe organic layer was separated
  6. washwashed with brine (100 mL)
  7. customThe organic layer was separated
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel flash chromatography
  12. washeluting with a gradient of 100% hexanes to 50% hexanes in EtOAc

出典と根拠

ORDレコード
ord-10e4397b61954dc79fd6e24d40645f4a
出典データセット
uspto-grants-2015_02
特許番号
US08952058B2

反応ノート

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