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Toluene → HCID 25260912, 화합물

HRID 1093299
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HRID 1093299 반응식
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13](Cl)[N:12]=[C:11]3[N:16]([CH:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)[N:17]=[CH:18][C:10]=13)[CH2:2]2.[C:31]1(C)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[NH2:38]OB(C1C=CC=CC=1)O.C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[NH2:38][C:31]1[CH:36]=[CH:35][C:34]([C:13]2[N:12]=[C:11]3[N:16]([CH:19]4[CH2:20][CH2:21][N:22]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]4)[N:17]=[CH:18][C:10]3=[C:9]([N:3]3[CH2:4][CH:5]4[O:8][CH:1]([CH2:7][CH2:6]4)[CH2:2]3)[N:14]=2)=[CH:33][CH:32]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 57227478HCID 57227478, 화합물HCID 86629384HCID 86629384, 화합물

생성물 1

HCID 25260912HCID 25260912, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

isopropyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate (680 mg, 1.56 mmol) was dissolved in ethanol (8 mL) and toluene (8 mL) and divided over two microwave vials. To each vial was added 1.3 eq of aminophenylboronic acid, pinacol ester (220 mg, 1 mmol to each vial) and a 2M aqueous solution of Na2CO3 (1.57 mL, 3.14 mmol, 4 eq. to each vial). The vials were purged with nitrogen gas and 10 mol % tetrakis(triphenylphosphine)palladium was added (91 mg to each vial). Each vial was heated under microwave irradiation for 60 minutes. The contents of both vials were combined, diluted with dichloromethane and water and filtered over Celite. The organic phase was washed with brine (2×), dried over MgSO4 and concentrated to give the product as an orange foam, which was used without further purification. MS: 492.3 [M+H], RT 2.31

후처리

  1. customThe vials were purged with nitrogen gas and 10 mol % tetrakis(triphenylphosphine)palladium
  2. additionwas added (91 mg to each vial)
  3. temperatureEach vial was heated under microwave irradiation for 60 minutes
  4. additiondiluted with dichloromethane and water
  5. filtrationfiltered over Celite
  6. washThe organic phase was washed with brine (2×)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cc26d16b1d834f75b14b3e9cc03ca8a2
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129371B2

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