Potassium Carbonate → HCID 68689963, compound

HRID 2244273Notes

Reaction equation

HRID 2244273 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].[S:35]1[CH:39]=[CH:38][CH:37]=[C:36]1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:34][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:2]=1[C:36]1[S:35][CH:39]=[CH:38][CH:37]=1)[C:6]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][N:11]2[C:19]([C:22]([NH:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[O:23])=[CH:20][CH:21]=[C:10]2[CH2:9]1)=[O:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339602-Thiopheneboronic acidHCID 15952466HCID 15952466, compound

Product 1

HCID 68689963HCID 68689963, compoundYield 123.7%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °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), 2-thiopheneboronic acid (0.102 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 90° C. for 4 hours. The cooled reaction mixture was 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, and concentrated in vacuo to give a brown syrup (0.34 g). Purification by flash chromatography using 280:8:1 dichloromethane:ethanol:aqueous ammonia as solvent gave an orange foam that was crystallized from diethyl ether/hexane to afford the title compound (0.168 g, 61%) as a tan solid.

Workup

  1. customwater (8 mL:2 mL) was purged with nitrogen for 10 minutes
  2. customThe cooled reaction mixture
  3. customwas 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. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d660231fecc64fab91650b73f5668bd9
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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