Sodium Carbonate → HCID 135856837, 화합물

HRID 1809200노트

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HRID 1809200 반응식
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

참가 물질

8

반응물 4

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

생성물 1

HCID 135856837HCID 135856837, 화합물

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-50cd3ad25ce943a99587b41f27034062
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362018B2

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