Triphenylphosphine → (R)-6-(2-(bromomethyl)-3-methylbutyl)-1-(3-methoxypropyl)-1H-indazole

HRID 660371Notes

Reaction equation

HRID 660371 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][C@H:16]([CH:19]([CH3:21])[CH3:20])[CH2:17]O)[CH:13]=2)[CH:8]=[N:7]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:48])C(=O)C1>C(Cl)Cl>[Br:48][CH2:17][C@@H:16]([CH:19]([CH3:21])[CH3:20])[CH2:15][C:12]1[CH:13]=[C:14]2[C:9]([CH:8]=[N:7][N:6]2[CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 68781374(R)-2-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutan-1-ol

Product 1

HCID 68783219(R)-6-(2-(bromomethyl)-3-methylbutyl)-1-(3-methoxypropyl)-1H-indazoleYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutan-1-ol (100 mg, 0.3 mmol) in dry CH2Cl2 (3 mL) at 0° C., Ph3P (140 mg, 0.6 mmol) and NBS (95 mg, 0.6 mmol) were added in portions. After stirring for 12 h at rt, the mixture was evaporated and the residue was purified by flash chromatography on silica gel to afford (R)-6-(2-(bromomethyl)-3-methylbutyl)-1-(3-methoxypropyl)-1H-indazole (70 mg, 62%). 1H NMR (400 MHz, CDCl3): 1.02 (m, 6H), 1.74 (m, 1H), 1.89 (m, 1H), 2.17 (m, 2H), 2.71 (m, 1H), 2.95 (m, 1H), 3.32 (s, 3H), 3.43 (m, 1H), 4.45 (m, 2H), 6.98 (d, 1H), 7.27 (s, 1H), 7.63 (d, 1H), 7.95 (s, 1H); MS: 432 (M++1)

Workup

  1. customthe mixture was evaporated
  2. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9a76586cabdb49b8b21b0b8986f3588e
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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