Cesium carbonate → HCID 59596595, compound

HRID 2264990Notes

Reaction equation

HRID 2264990 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH2:16])=[O:5])[CH3:2].[CH:17]1([C:20]2[CH:25]=[CH:24][C:23](I)=[C:22]([F:27])[CH:21]=2)[CH2:19][CH2:18]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:23]1[CH:24]=[CH:25][C:20]([CH:17]2[CH2:19][CH2:18]2)=[CH:21][C:22]=1[F:27])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59596525HCID 59596525, compoundHCID 595966234-Cyclopropyl-2-fluoro-1-iodobenzene

Product 1

HCID 59596595HCID 59596595, compoundYield 23.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A degassed solution of 3-amino-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (521 mg, 2.4 mmol), 4-cyclopropyl-2-fluoro-1-iodo-benzene (810 mg, 3.09 mmol), Pd2dba3 (154 mg, 0.168 mmol), Xantphos (194 mg, 0.336 mmol) and cesium carbonate (1.95 g, 6.0 mmol) in toluene (5 ml) was heated at 110° C. for 18 hours. The reaction mixture was cooled to ambient temperature then filtered through a pad of Celite®. The filtrate was washed with water and brine, dried over magnesium sulphate and concentrated in vacuo to give a brown gum. The gum was purified by flash chromatography (Si-PPC, DCM:MeOH, 90:10) to provide the title compound as an orange oil (197 mg, 23%). LCMS (method B): RT=2.65 min, M+H+=354.

Workup

  1. filtrationthen filtered through a pad of Celite®
  2. washThe filtrate was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customto give a brown gum
  6. customThe gum was purified by flash chromatography (Si-PPC, DCM:MeOH, 90:10)

Sources & evidence

ORD record
ord-9c6e571dce80496b8c0f799cd2d78202
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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