Cesium carbonate → HCID 57637383, compound

HRID 2078731Notes

Reaction equation

HRID 2078731 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[C:10]([Br:18])=[C:9]1[C:19]1[C:20]2[S:33][CH:32]=[CH:31][C:21]=2[N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[N:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+]>BrCCCBr>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:19][CH2:9][CH2:10][Br:18])[CH:15]=2)[C:10]([Br:18])=[C:9]1[C:19]1[C:20]2[S:33][CH:32]=[CH:31][C:21]=2[N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[N:23]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 136016240HCID 136016240, compound2×

Product 1

HCID 57637383HCID 57637383, compoundYield 144.9%

Reagents, catalysts & solvents 1

HCID 80011,3-DibromopropaneSolvent

Conditions

Temperature
75 °C

Procedure

To 3-bromo-2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-6-hydroxy-indole-1-carboxylic acid tert-butyl ester [0.22 g, 0.40 mmol, Intermediate (65)] in 1,3 dibromopropane (4 mL) was added cesium carbonate (0.33 g, 1.0 mmol). The resulting suspension was stirred at 75° C. for 1 hour then filtered. The insoluble was filtered off. The filtrate was concentrated. The residue was chromatographed through silica gel (n-heptane/ethyl acetate, 100/0 then 90/10) to provide 3-bromo-6-(3-bromo-propoxy)-2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-indole-1-carboxylic acid tert-butyl ester [0.19 g, 72%, Intermediate (66)] as a white foam. LC/MS: 654.0 (M+H), RT=4.71 minutes.

Workup

  1. filtrationthen filtered
  2. filtrationThe insoluble was filtered off
  3. concentrationThe filtrate was concentrated
  4. customThe residue was chromatographed through silica gel (n-heptane/ethyl acetate, 100/0

Sources & evidence

ORD record
ord-0a39c487efd54312907042f29bdcb3f6
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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