Sodium borohydride → 5-(5-fluoro-4-(hydroxymethyl)pyridin-3-yl)-3-methylbenzo[d]oxazol-2(3H)-one

HRID 1253949노트

반응식

HRID 1253949 반응식
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][C:18](=[O:20])[N:17]([CH3:21])[C:16]=3[CH:22]=2)[C:9]=1[CH:10]=[O:11]>C1COCC1.O.[Cl-].[Na+].O.C(Cl)Cl>[F:3][C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][C:18](=[O:20])[N:17]([CH3:21])[C:16]=3[CH:22]=2)[CH:7]=[N:6][CH:5]=1

참가 물질

7

반응물 2

HCID 4311764Sodium borohydrideHCID 86663361HCID 86663361, 화합물

생성물 1

HCID 667977725-(5-fluoro-4-(hydroxymethyl)pyridin-3-yl)-3-methylbenzo[d]oxazol-2(3H)-one수율 16%

시약·촉매·용매 4

HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

Sodium borohydride (6.3 mg, 0.17 mmol) was added to a solution of 3-Fluoro-5-(3-methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-4-carbaldehyde (47 mg, 0.17 mmol) in THF (0.5 mL) and water (0.1 mL) at 0° C. The resulting mixture was stirred at room temperature for 2 h. Brine was added to the reaction mixture. The resulting mixture was diluted with DCM and water. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-3%) and afforded the title compound (7 mg, 16%); ESI-MS m/z: 275 [M+1]+, Retention time 0.92 min; 1HNMR (MeOD, 400.3 MHz) δ 3.44 (s, 3H), 4.59 (s, 2H), 7.32 (dd, J=8.0, 1.2 Hz, 1H), 7.35 (d, J=1.2 Hz, 1H), 7.38 (d, J=80 Hz, 1H), 8.39 (s, 1H), 8.48 (d, J=1.2 Hz, 1H).

후처리

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-3%)

출처 및 근거

ORD 기록
ord-c23cc2869bba4fd9bb134b68721492e7
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455522B2

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