Potassium Carbonate → HCID 54518398, compound

HRID 1791776Notes

Reaction equation

HRID 1791776 reaction equation
[C:1]([O:4][C@H:5]([CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](Cl)=[N:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:19][CH3:20])(=[O:3])[CH3:2].[F:27][C:28]1[C:36]([OH:37])=[CH:35][CH:34]=[C:33]2[C:29]=1[CH:30]=[C:31]([CH3:38])[NH:32]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([O:4][C@H:5]([CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([O:37][C:36]3[C:28]([F:27])=[C:29]4[C:33](=[CH:34][CH:35]=3)[NH:32][C:31]([CH3:38])=[CH:30]4)=[N:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:19][CH3:20])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 103520364-fluoro-2-methyl-1H-indol-5-olHCID 54212641HCID 54212641, compound

Product 1

HCID 54518398HCID 54518398, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of (2R)-7-(2-acetoxy-3-(pyrrolidin-1-yl)propoxy)4-chloro-6-methoxyquinazoline (530 mg, 1.4 mmol) and 4-fluoro-5-hydroxy-2-methylindole (277 mg, 1.68 mmol), (prepared as described for the starting material in Example 237), in DMF (8 ml) containing potassium carbonate (290 mg, 2.1 mmol) was stirred at 90° C. for 2 hours. After cooling, the volatiles were removed under vacuum and the residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give (2R)-7-(2-acetoxy-3-(pyrrolidin-1-yl)propoxy)-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxyquinazoline (580 mg, 81%).

Workup

  1. custom(prepared
  2. temperatureAfter cooling
  3. customthe volatiles were removed under vacuum
  4. customthe residue was purified by column chromatography
  5. washeluting with methylene chloride/methanol (95/5)

Sources & evidence

ORD record
ord-15520b7aa20a499bbf62226c8aec6142
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

Loading…