Water → (2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl) methanol

HRID 1776852Notes

Reaction equation

HRID 1776852 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:18][CH:17]([C:19](OCC)=[O:20])[N:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[C:13]([F:16])[C:14]=4[CH:15]=[C:7]3[C:6]=2[N:24]=1.[BH4-].[Na+].O>CO.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:18][CH:17]([CH2:19][OH:20])[N:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[C:13]([F:16])[C:14]=4[CH:15]=[C:7]3[C:6]=2[N:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86728253ethyl 2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole-6-carboxylate

Product 1

HCID 86728254(2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl) methanolYield 95.5%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of ethyl 2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-6-carboxylate (3 g, 8.73 mmol) and NaBH4 (1.58 g, 43.67 mmol) in CH3OH/dichloromethane (30 mL/10 mL) was stirred at room temperature for 2 hours. The mixture was poured to H2O and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to provide (2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-6-yl)methanol (2.54 g, yield: 95.5%). 1H-NMR (DMSO-d6, 400 MHz) δ 7.60 (d, J=8.8 Hz, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 7.22˜7.28 (m, 1H), 7.08 (s, 1H), 6.94 (dd, J=10.4, 8.4 Hz, 1H), 6.78 (t, J=4.0 Hz, 1H), 5.29 (t, J=6.0 Hz, 1H), 3.71˜3.78 (m, 1H), 3.61˜3.67 (m, 1H). MS (M+H)+: 305.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f596deb98be54980996b7a2068a77975
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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