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

HRID 1776861Notes

Reaction equation

HRID 1776861 reaction equation
[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:21]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>N1C=CC=CC=1>[CH3:22][S:23]([O:20][CH2:19][CH:17]1[N:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([F:16])[C:14]=3[CH:15]=[C:7]2[C:6]2[N:21]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:18]1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 86728254(2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl) methanol

Product 1

HCID 86728265(2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl methanesulfonateYield 95.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-6-yl)methanol (1.00 g, 3.29 mmol) in dry pyridine (10 mL) at room temperature was added dropwise MsCl (1.23 g, 10.74 mmol) at 0° C. Then the reaction mixture was stirred at room temperature for 2 hours under N2 protection. The reaction was poured into water and filtered. The filter cake was washed with water and dried to provide (2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl methanesulfonate (1.20 g, yield: 90.1%). 1H-NMR (DMSO-d6, 400 MHz) δ 7.37˜7.51 (m, 2H), 7.28˜7.33 (m, 2H), 7.18˜7.24 (d, J=8.4 Hz, 1H), 6.9-6.98 (m, 1H), 6.65˜6.72 (m, 1H), 4.46˜4.53 (m, 1H), 4.31˜4.38 (m, 1H), 2.90 (s, 3H). MS (M+H)+: 383.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with water
  3. customdried

Sources & evidence

ORD record
ord-8bd1ec1d85da42138ccb313629bb2a27
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

Loading…