Dimethylformamide → HCID 18318477, compound

HRID 1700775Notes

Reaction equation

HRID 1700775 reaction equation
Br[C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]2[C:8]3[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=3[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.CN([CH:40]=[O:41])C>>[N:32]1([C:40]([C:2]2[CH:3]=[CH:4][C:5]([CH2:6][C:7]3[C:8]4[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=4[S:10][C:11]=3[C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)=[CH:16][CH:17]=3)=[CH:30][CH:31]=2)=[O:41])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 18318446HCID 18318446, compound

Product 1

HCID 18318477HCID 18318477, compound

Conditions

Temperature
80 °C

Procedure

3-(4-Bromobenzyl)-2-[4-[2-(1-pyrrolidinyl)ethoxy]-phenyl]benzo[b]thiophene (178 mg, 0.36 mmol) was dissolved in DMF (2.0 mL) and treated with pyrrolidine (0.3 mL). The solution was purged with carbon monoxide for 5 min at 80° C. before the catalyst dichlorobis(triphenylphosphine)pallidium (10 mg) was added. The reaction mixture was allowed to stir under a balloon of carbon monoxide at 80° C. for 4 h, then diluted with brine (30 mL) and extracted with EtOAc (20 mL×3). The combined organic layers were dried with sodium sulfate and concentrated. Chromotography with Et3N:MeOH:EtOAc (5:5:90) afforded the product (16 mg) along with recovered starting material (140 mg). FDMS m/e: found 511 (M+H+); 1H NMR (CDCl3): δ 7.97 (d, 1H), 7.57 (m, 1H), 7.55 (d, 2H), 7.50 (m, 1H), 7.40 (m, 1H), 7.39 (d, 2H), 7.24 (d, 2H), 7.03 (d, 2H), 4.40 (s, 2H), 4.28 (t, 2H), 3.76 (t, 2H), 3.57 (t, 2H), 3.10 (t, 2H), 2.82 (m, 4H), 2.01 (m, 4H), 1.98 (m, 4H).

Workup

  1. customThe solution was purged with carbon monoxide for 5 min at 80° C. before the catalyst dichlorobis(triphenylphosphine)pallidium (10 mg)
  2. additionwas added
  3. additiondiluted with brine (30 mL)
  4. extractionextracted with EtOAc (20 mL×3)
  5. dry with materialThe combined organic layers were dried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f298284664d1464c84d8a4b0a08adfec
Source dataset
uspto-grants-2002_02
Patent number
US06350774B1

Reaction notes

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