Potassium Carbonate → HCID 68687850, compound

HRID 2244250Notes

Reaction equation

HRID 2244250 reaction equation
I[C:2]1[CH:33]=[CH:32][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[C:19]([C:22]([NH:24][CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)=[O:23])=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][C:3]=1[CH3:34].[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC>[CH3:34][C:3]1[CH:4]=[C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[C:19]([C:22]([NH:24][CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)=[O:23])=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])[CH:32]=[CH:33][C:2]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 15952466HCID 15952466, compound

Product 1

HCID 68687850HCID 68687850, compoundYield 117.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 10-(4-iodo-3-methylbenzoyl)-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 74 (0.300 g, 0.53 mmol), phenylboronic acid (0.098 g, 0.80 mmol) and potassium carbonate (0.221 g, 1.60 mmol) in dimethoxyethane:water (8 mL:2 mL) was purged with nitrogen for 10 minutes. [1,1′-bis(Diphenylphosphino)ferrocene]dichloropalladium[II] (0.022 g, 0.0266 mmol) was then added and the reaction mixture heated to 100° C. for 4 hours. The cooled reaction mixture was then partitioned between ethyl acetate (100 mL) and 1 M sodium hydroxide (100 mL). The organic phase was separated, washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give an olive syrup (0.32 g). Purification by flash chromatography using ethyl acetate as solvent afforded the title compound (0.260 g, 95%) as a white foam, m.p. 108-112° C.

Workup

  1. customwater (8 mL:2 mL) was purged with nitrogen for 10 minutes
  2. customThe cooled reaction mixture
  3. customwas then partitioned between ethyl acetate (100 mL) and 1 M sodium hydroxide (100 mL)
  4. customThe organic phase was separated
  5. washwashed with water (100 mL) and brine (100 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b04cac75e5484f5a9f7d368124d514ef
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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