Carbon tetrabromide → 2-(4-(Bromomethyl)-2-nitrophenyl)-5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine

HRID 1177519Notes

Reaction equation

HRID 1177519 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:28]O)[CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20]1)[N:13]=2)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:50]>C(Cl)Cl>[Br:50][CH2:28][C:6]1[CH:7]=[CH:8][C:9]([C:10]2[S:11][C:12]3[C:17]([N:18]=2)=[CH:16][CH:15]=[C:14]([C:19]2([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:20][CH2:21]2)[N:13]=3)=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67111784(3-Nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methanol

Product 1

HCID 671118432-(4-(Bromomethyl)-2-nitrophenyl)-5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a nearly clear solution of (3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methanol (0.394 g, 0.977 mmol) and triphenyl phosphine (0.294 mL, 1.27 mmol) in 10 mL DCM at 0° C. was added carbon tetrabromide (0.114 mL, 1.17 mmol) in one portion. The reaction mixture was allowed to stir 1 h, then was treated with 3.5 g silica gel and dried. Purification by silica gel chromatography, 40 g, 0-30% EA/hexanes gave 2-(4-(bromomethyl)-2-nitrophenyl)-5-(1-phenylcyclopropyl)thiazolo-[5,4-b]pyridine as an orange-yellow solid. MS (ESI) m/z: Calculated: 467.0; Observed: 467.6 (M++1).

Workup

  1. additionwas treated with 3.5 g silica gel
  2. customdried
  3. customPurification by silica gel chromatography, 40 g, 0-30% EA/hexanes

Sources & evidence

ORD record
ord-145802f2e18d49db9c033dc9b3e987f2
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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