Boron tribromide → 3-Methyl-4-(5-thiophen-3-yl-thiazol-2-ylamino)-phenol

HRID 1713676Notes

Reaction equation

HRID 1713676 reaction equation
N1(CCOC2C=CC(NC3SC(C4C=CC(O)=CC=4)=CN=3)=CC=2)CCCC1.C[O:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37]2[S:38][C:39]([C:42]3[CH:46]=[CH:45][S:44][CH:43]=3)=[CH:40][N:41]=2)=[C:32]([CH3:47])[CH:31]=1.B(Br)(Br)Br>C(Cl)Cl.CO>[CH3:47][C:32]1[CH:31]=[C:30]([OH:29])[CH:35]=[CH:34][C:33]=1[NH:36][C:37]1[S:38][C:39]([C:42]2[CH:46]=[CH:45][S:44][CH:43]=2)=[CH:40][N:41]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 111882064-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-thiazol-5-yl}-phenolHCID 58923520(4-Methoxy-2-methyl-phenyl)-(5-thiophen-3-yl-thiazol-2-yl)-amine

Product 1

HCID 589235083-Methyl-4-(5-thiophen-3-yl-thiazol-2-ylamino)-phenol

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound is prepared as described in Example 7 for 4-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-thiazol-5-yl}-phenol but starting from (4-methoxy-2-methyl-phenyl)-(5-thiophen-3-yl-thiazol-2-yl)-amine and using 4 equivalents of BBr3. Title compound: ES-MS: 289.0 [M+H]+; single peak at tR=3.33 min (System 2); Rf=0.15 (CH2Cl2/MeOH, 95/5).

Workup

  1. customThe title compound is prepared

Sources & evidence

ORD record
ord-8fb96b38c221475190b3f03e52f0f76c
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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