Sodium Carbonate → HCID 15953847, compound

HRID 1877972Notes

Reaction equation

HRID 1877972 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]1[N:16]2[CH:17]=[N:18][CH:19]=[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11]1)[C:5]#[N:6].C(=O)([O-])[O-].[Na+].[Na+].[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[C:9]([CH:10]3[N:16]4[CH:17]=[N:18][CH:19]=[C:15]4[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 58827202HCID 58827202, compound

Product 1

HCID 15953847HCID 15953847, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To 3-bromo-4-(6,7,8,9-tetrahydro-5H-imidazo[1,5-a]azepin-5-yl)benzonitrile (0.507 g, 1.59 mmol) is added DME (7.0 mL). To this is added aqueous 2M sodium carbonate (3.0 mL, 6 mmol) followed by 4-fluorophenylboronic acid (0.552 g, 3.97 mmol). This mixture is transferred to a microwave safe vial. Tetrakis(triphenylphosphine) palladium(0) (0.03 g, 0.025 mmol) is added, and the vessel sealed. The mixture is stirred briefly (30 seconds) and placed in a microwave for 25 minutes at 125° C. The vial is allowed to cool and unsealed. The mixture is extracted into ethyl acetate and washed with saturated sodium bicarbonate. The organic layer is removed in vacuo. The resulting material is subjected to chromatography (Silica gel, 1:50 to 1:25 methanol:methylene chloride) to give the desired product. MS (ESI) m/z 332 (M+H)

Workup

  1. customthe vessel sealed
  2. waitplaced in a microwave for 25 minutes at 125° C
  3. temperatureto cool
  4. extractionThe mixture is extracted into ethyl acetate
  5. washwashed with saturated sodium bicarbonate
  6. customThe organic layer is removed in vacuo

Sources & evidence

ORD record
ord-65dd67b765ef4c31ac061a5456d1e145
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

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