Sodium borohydride → N-(2,4-difluorophenyl)-8-(hydroxymethyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

HRID 628116노트

반응식

HRID 628116 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH3:27])[C:10]([C:12]1[S:24][C:23]2[C:22]3[CH:21]=[C:20]([CH:25]=[O:26])[CH:19]=[CH:18][C:17]=3[O:16][CH2:15][C:14]=2[CH:13]=1)=[O:11].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH3:27])[C:10]([C:12]1[S:24][C:23]2[C:22]3[CH:21]=[C:20]([CH2:25][OH:26])[CH:19]=[CH:18][C:17]=3[O:16][CH2:15][C:14]=2[CH:13]=1)=[O:11]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 57900416N-(2,4-difluorophenyl)-8-formyl-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

생성물 1

HCID 57900161N-(2,4-difluorophenyl)-8-(hydroxymethyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To an ice-cooled solution of N-(2,4-difluorophenyl)-8-formyl-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide in ethanol (1 mL) was added sodium borohydride (10 mg, 0.3 mmol, 6 equiv). After 3 hr, excess sodium borohydride was quenched with saturated aqueous ammonium chloride solution (3 mL). The ethanol was removed in vacuo, and the resulting aqueous solution was extracted with ethylacetate (3×3 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (3:2 hexanes/ethylacetate) provided 159bp (5.2 mg, 30%). 1H NMR (500 MHz, CDCl3) δ 7.26 (m, 1H), 7.15 (m, 1H), 7.05 (m, 1H), 6.86-6.93 (m, 4H), 5.25 (s, 2H), 4.55 (d, J=6.7 Hz, 2H), 4.06 (m, 1H), 3.40 (s, 3H). LCMS (ESI) m/z: 388.1.

후처리

  1. customexcess sodium borohydride was quenched with saturated aqueous ammonium chloride solution (3 mL)
  2. customThe ethanol was removed in vacuo
  3. extractionthe resulting aqueous solution was extracted with ethylacetate (3×3 mL)
  4. dry with materialThe collected organic was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (3:2 hexanes/ethylacetate)
  8. customprovided 159bp (5.2 mg, 30%)

출처 및 근거

ORD 기록
ord-3bb1b5c515fe42aa98d5a9552dcb94f7
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309265B2

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