1-Bromopropane → HCID 11461093, compound

HRID 749506Notes

Reaction equation

HRID 749506 reaction equation
Br[CH2:2][CH2:3][CH3:4].[C:5]1([S:11][C:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[NH:14][C:13]=2[C:21]([NH2:23])=[O:22])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([O-])([O-])=O.[Cs+].[Cs+]>N1C=CC=CC=1>[C:5]1([S:11][C:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[N:14]([CH2:2][CH2:3][CH3:4])[C:13]=2[C:21]([NH2:23])=[O:22])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 10796Cesium carbonateHCID 11482594HCID 11482594, compound

Product 1

HCID 11461093HCID 11461093, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add 1-bromopropane (19 mg, 0.154 mmol) at r.t. to a mixture of 3-phenylsulfanyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid amide (Ia-1, 31.5 mg, 0.12 mmol), Cs2CO3 (60 mg, 0.185 mmol) in pyridine (0.5 ml). Heat the reaction at 80° C. in a sealed vessel for 1 hr. Cool the mixture and extract into ethyl acetate from water. Separate the organic phase and evaporate. Purify the residue (33 mg) by flash chromatography (SiO2, 2 gm, elute with heptane:DCM then MeOH 0-4% in DCM) to provide title compound (11.5 mg) as a white solid, 1H NMR (CDCl3) and LC-MS (m/e=311) are consistent for the title compound structure.

Workup

  1. temperatureHeat
  2. customthe reaction at 80° C. in a sealed vessel for 1 hr
  3. temperatureCool the mixture
  4. extractionextract into ethyl acetate from water
  5. customSeparate the organic phase
  6. customevaporate
  7. customPurify the residue (33 mg) by flash chromatography (SiO2, 2 gm
  8. washelute with heptane

Sources & evidence

ORD record
ord-fa83322a93e44af097c2126f00318b17
Source dataset
uspto-grants-2008_07
Patent number
US07402672B2

Reaction notes

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