Sodium Carbonate → HCID 135856837, compound

HRID 1809200Notes

Reaction equation

HRID 1809200 reaction equation
Br[C:2]1[N:6]2[CH:7]=[C:8](Br)[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][CH:3]=1.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:46](C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1P(C1C=CC=CC=1)C1C=CC=CC=1>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[OH:46][C:47]1[CH:52]=[CH:51][C:50]([C:2]2[N:6]3[CH:7]=[C:8]([C:32]4[CH:33]=[CH:34][C:35]([OH:38])=[CH:36][CH:37]=4)[N:9]=[C:10]([NH:11][CH2:12][C:13]4[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=4)[C:5]3=[N:4][CH:3]=2)=[CH:49][CH:48]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 25205707HCID 25205707, compound

Product 1

HCID 135856837HCID 135856837, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A microwave tube was charged with 4-[(3,6-Dibromo-imidazo[1,2-a]pyrazin-8-ylamino)-methyl]-benzenesulfonamide (0.17 g, 0.379 mmol), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (0.175 g, 0.79 mmol), Na2CO3 (0.10 g, 0.95 mmol), Pd(OAc)2 (7 mg, 0.028 mmol), and (Oxidi-2,1-phenylene)bis(diphenylphosphine) (20 mg, 0.0379 mmol), suspended in a mixture of DMF (3 mL) and water (1 ml). The tube was sealed under a nitrogen atmosphere then heated to 130° C. for 20 min. The reaction was filtered, diluted with AcOEt and washed with water. The organic layer was dried with MgSO4 anh. filtered and evaporated. The crude mixture was purified by prep. HPLC under acid conditions using a gradient of 0.1% formic acid in H2O/0.1% formic acid in Acetonitrile (95/5:5 min, 9/1:13 min, 0/1:4 min) to give 4-{[3,6-Bis-(4-hydroxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide as a brown solid (21 mg,). LC-MS m/z 488 [M+H]+.

Workup

  1. customThe tube was sealed under a nitrogen atmosphere
  2. filtrationThe reaction was filtered
  3. additiondiluted with AcOEt
  4. washwashed with water
  5. dry with materialThe organic layer was dried with MgSO4 anh. filtered
  6. customevaporated
  7. customThe crude mixture was purified by prep
  8. customa gradient of 0.1% formic acid in H2O/0.1% formic acid in Acetonitrile (95/5:5 min, 9/1:13 min, 0/1:4 min)

Sources & evidence

ORD record
ord-50cd3ad25ce943a99587b41f27034062
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

Loading…