Potassium Carbonate → HCID 86726457, compound

HRID 529685Notes

Reaction equation

HRID 529685 reaction equation
Cl[C:2]1[N:3]=[C:4]([O:29][CH:30]2[CH2:32][CH2:31]2)[C:5]2[C:10]([C:11]3[CH:20]=[CH:19][C:14]4[N:15]=[C:16]([CH3:18])[O:17][C:13]=4[CH:12]=3)=[CH:9][N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:6]=2[N:7]=1.[NH2:33][C:34]1[CH:43]=[CH:42][C:37]([C:38]([NH:40][CH3:41])=[O:39])=[CH:36][C:35]=1[O:44][CH3:45].C(=O)([O-])[O-].[K+].[K+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:30]1([O:29][C:4]2[C:5]3[C:10]([C:11]4[CH:20]=[CH:19][C:14]5[N:15]=[C:16]([CH3:18])[O:17][C:13]=5[CH:12]=4)=[CH:9][N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:6]=3[N:7]=[C:2]([NH:33][C:34]3[CH:43]=[CH:42][C:37]([C:38]([NH:40][CH3:41])=[O:39])=[CH:36][C:35]=3[O:44][CH3:45])[N:3]=2)[CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 204444344-Amino-3-methoxy-N-methylbenzamideHCID 867264566-(2-Chloro-4-cyclopropoxy-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole

Product 1

HCID 86726457HCID 86726457, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-(2-chloro-4-cyclopropoxy-7-((2-(trimethylsilyl)- ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole (1 equiv), 4-amino-3-methoxy-N-methylbenzamide (2 equiv), potassium carbonate (3.5 equiv), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.23 equiv), tris(dibenzylideneacetone)dipalladium (0.23 equiv) in 1,4-dioxane (0.085 M) was purged with nitrogen and sealed. The reaction mixture was heated to 140° C. for 1.5 h. After cooling to room temperature the reaction mixture was purified using flash chromatography (0-100% ethyl acetate in hexane then 0-20% methanol in DCM) eluted with 17% methanol in DCM to give the title compound (57.5% yield) as brown oil. MS (ESI) m/z 615.4 [M+1]+.

Workup

  1. customwas purged with nitrogen
  2. customsealed
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. customwas purified
  5. wash0-20% methanol in DCM) eluted with 17% methanol in DCM

Sources & evidence

ORD record
ord-45bdf43ac0094f7ebe404fad2765c952
Source dataset
uspto-grants-2016_05
Patent number
US09346812B2

Reaction notes

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