Isopropanol → 2-(3-chloro-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinolin-1(2H)-one

HRID 2069708ノート

反応式

HRID 2069708 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([F:23])[CH:14]=[C:15]([CH:20]4[CH2:22][CH2:21]4)[CH:16]=3)[C:11]2=[O:24])[C:3]=1[CH:4]=[O:5].CC(O)C.[BH4-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[C:6]([N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([F:23])[CH:14]=[C:15]([CH:20]4[CH2:22][CH2:21]4)[CH:16]=3)[C:11]2=[O:24])[CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 594737722-chloro-6-(6-cyclopropyl-8-fluoro-1-oxoisoquinolin-2(1H)-yl)benzaldehyde

生成物 1

HCID 594737982-(3-chloro-2-(hydroxymethyl)phenyl)-6-cyclopropyl-8-fluoroisoquinolin-1(2H)-one収率 86.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-chloro-6-(6-cyclopropyl-8-fluoro-1-oxoisoquinolin-2(1H)-yl)benzaldehyde (64.6 g, 0.19 mol) was dissolved in DCM (650 ml), then, IPA (325 ml) was added to the solution. At 4° C., NaBH4 (7.15 g, 0.19 mol) was added to the reaction mixture portion wise, then the resulting solution was stirred for 1 hr. The reaction was quenched by water (170 mL), then the mixture was filtered through Celite pad. DCM layer was collected by phase separation, and DCM was distilled out and IPA was added in the same time. The desired product was crystallized out from IPA, collected by filtration, and washed with cold IPA. The filter cake was dried under vacuum at 70° C. to afford 56.3 g of the title compound (86.6% isolated yield) as a white solid. MS (ESI) 343, 345 (M+H)+.

後処理

  1. customThe reaction was quenched by water (170 mL)
  2. filtrationthe mixture was filtered through Celite pad
  3. customDCM layer was collected by phase separation, and DCM
  4. distillationwas distilled out and IPA
  5. additionwas added in the same time
  6. customThe desired product was crystallized out from IPA
  7. filtrationcollected by filtration
  8. washwashed with cold IPA
  9. customThe filter cake was dried under vacuum at 70° C.

出典と根拠

ORDレコード
ord-4ef5b316c5fe40c996c4ecca005aa5f9
出典データセット
uspto-grants-2012_10
特許番号
US08299077B2

反応ノート

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