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

HRID 1253949ノート

反応式

HRID 1253949 の反応式
[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

参加物

7

反応物 2

HCID 4311764Sodium borohydrideHCID 86663361HCID 86663361、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-c23cc2869bba4fd9bb134b68721492e7
出典データセット
uspto-grants-2013_06
特許番号
US08455522B2

反応ノート

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