Toluene → HCID 25260912, compound

HRID 1093299Notes

Reaction equation

HRID 1093299 reaction equation
[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

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 57227478HCID 57227478, compoundHCID 86629384HCID 86629384, compound

Product 1

HCID 25260912HCID 25260912, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-cc26d16b1d834f75b14b3e9cc03ca8a2
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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