Boron tribromide → 3-{[3-(4-Hydroxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide

HRID 1809178Notes

Reaction equation

B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]3[CH:18]=[CH:19][N:20]=[C:21]([NH:22][CH2:23][C:24]4[CH:25]=[C:26]([S:30]([NH2:33])(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=4)[C:16]3=[N:15][CH:14]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:17]3[CH:18]=[CH:19][N:20]=[C:21]([NH:22][CH2:23][C:24]4[CH:25]=[C:26]([S:30]([NH2:33])(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=4)[C:16]3=[N:15][CH:14]=2)=[CH:11][CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

BBr3 (2.81 mL, 1.0M in DCM, 2.81 mmol) is added to a suspension of 3-{[3-(4-Methoxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide (0.115 g, 0.281 mmol) in DCM (3 mL) at −78° C. under nitrogen atmosphere. The reaction is allowed to warm to r.t and monitored by analytical HPLC. After 2 h the reaction is complete and is cooled to −78° C., quenched with a solution of saturated aqueous K2CO3. The reaction is diluted with AcOEt, washed with water, dried with MgSO4 anh., filtered and evaporated to give 0.058 g of 3-{[3-(4-Hydroxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide as a brown oil (52%). No further purification was required. LC-MS m/z 396 [M+H]+.

Workup

temperatureto warm to r.t and
customquenched with a solution of saturated aqueous K2CO3
additionThe reaction is diluted with AcOEt
washwashed with water
dry with materialdried with MgSO4 anh.
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-d3c09daa8f024e968ab90eae0bad94b2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362018B2

Reaction notes

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