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

HRID 660367Notes

Reaction equation

HRID 660367 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]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:43])C(=O)C1>C(Cl)Cl>[Br:43][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 68502114(1-(3-methoxypropyl)-1H-indazol-6-yl)methanol

Product 1

HCID 687838246-(bromomethyl)-1-(3-methoxypropyl)-1H-indazoleYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-(3-methoxypropyl)-1H-indazol-6-yl)methanol (660 mg, 3 mmol) in dry CH2Cl2 (15 mL) at 0° C., Ph3P (943 mg, 3.6 mmol) and NBS (640 mg, 3.6 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 give 6-(bromomethyl)-1-(3-methoxypropyl)-1H-indazole (420 mg, 50%). 1H NMR (400 MHz, CDCl3): 2.18 (m, 2H), 3.26 (m, 2H), 3.31 (s, 3H), 4.49 (m, 2H), 4.65 (s, 2H), 7.18 (m, 1H), 7.48 (s,1H), 7.79 (m,1H), 7.99 (m,1H)

Workup

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

Sources & evidence

ORD record
ord-f2a76d6ff56b4f179f1814d2c7f86eba
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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