Boron tribromide → 4-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-thiazol-5-yl}-phenol

HRID 1713646Notes

Reaction equation

HRID 1713646 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:17][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:21][CH:20]=3)=[N:15][CH:14]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[N:28]1([CH2:27][CH2:26][O:25][C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:16]3[S:17][C:13]([C:10]4[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=4)=[CH:14][N:15]=3)=[CH:24][CH:23]=2)[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11188635[5-(4-Methoxy-phenyl)-thiazol-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Product 1

HCID 111882064-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-thiazol-5-yl}-phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1 N solution of BBr3 in CH2Cl2 (0.4 mL, 0.404 mmol, 8.0 equiv) is added dropwise to a cold (−10° C.) solution of [5-(4-methoxy-phenyl)thiazol-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (Example 3) (20 mg, 0.0506 mmol) in CH2Cl2 (0.4 mL), under an argon atmosphere. The reaction mixture is allowed to warm to RT and to stir for 1.5 h. The mixture is then cooled to 0° C. and quenched with MeOH. The resulting red solution is concentrated in vacuo. Purification of the crude material by silica gel (9 g) column chromatography (CH2Cl2/MeOH, 90/10) affords the title compound as a beige solid: ES-MS: 382.0 [M+H]+; single peak at tR=5.47 min (System 1); Rf=0.28 (CH2Cl2/MeOH, 80/20).

Workup

  1. temperatureThe mixture is then cooled to 0° C.
  2. customquenched with MeOH
  3. concentrationThe resulting red solution is concentrated in vacuo
  4. customPurification of the crude material by silica gel (9 g) column chromatography (CH2Cl2/MeOH, 90/10)

Sources & evidence

ORD record
ord-33a4df9b4055415f8214a97eb4306892
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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