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

HRID 1809182Notes

Reaction equation

Br[C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[C:5]2=[N:4][C:3]=1C.CC1(C)C(C)(C)OB([C:32]2[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[OH:38][C:35]1[CH:36]=[CH:37][C:32]([C:2]2[N:6]3[CH:7]=[CH:8][N:9]=[C:10]([NH:11][CH2:12][C:13]4[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:17][CH:18]=4)[C:5]3=[N:4][CH:3]=2)=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a 5 mL microwave tube is added 4-[(3-Bromo-2-methyl-imidazo[1,2-a]pyrazin-8-ylamino)-methyl]-benzenesulfonamide (0.15 g, 0.379 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (0.084 g, 0.417 mmol), Na2CO3 (0.1 g, 0.95 mmol), Pd(OAc)2 (approx. 7 mg, 0.028 mmol), and (oxidi-2,1-phenylene)bis(diphenylphosphine) (20 mg, 0.038 mmol). The mixture is suspended in DMF (3 mL) and water (1 mL) and the vessel is sealed under a nitrogen atmosphere. The reaction vessel is heated to 130° C. in the CEM microwave for 20 min then allowed to cool and filtered through Celite and washed with EtOAc. The filtrate is evaporated and the residue is taken up in DMSO and purified by prep HPLC. The product, 4-{[3-(4-Hydroxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide, is obtained as a white solid (15 mg, 10%) LC-MS m/z 410 [M+H]+.

Workup

temperatureto cool
filtrationfiltered through Celite
washwashed with EtOAc
customThe filtrate is evaporated
custompurified by prep HPLC

Sources & evidence

ORD record: ord-23b91581db774d49bec21b68c053e5aa
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362018B2

Reaction notes

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