2,5-Dibromo-thieno[3,2-b]furan → 4-(2-bromo-thieno[3,2-b]furan-5-yl)-(S)-2-(1-tert-butoxycarbonyl-pyrrolidin-2-yl)-imidazole-1-carboxylic acid tert-butyl ester

HRID 716548Notes

Reaction equation

HRID 716548 reaction equation
[Br:1][C:2]1[O:6][C:5]2[CH:7]=[C:8](Br)[S:9][C:4]=2[CH:3]=1.[C:11]([O:15][C:16]([N:18]1[C:22]([Sn](CCCC)(CCCC)CCCC)=[CH:21][N:20]=[C:19]1[C@@H:36]1[CH2:40][CH2:39][CH2:38][N:37]1[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(OC(N1CCC[C@H]1C1NC(C2SC3C=C(C4C=CC(C5NC([C@@H]6CCCN6C(=O)[C@@H](NC(OC)=O)C(C)C)=NC=5)=CC=4)SC=3C=2)=CN=1)=O)(C)(C)C>>[C:11]([O:15][C:16]([N:18]1[CH:22]=[C:21]([C:8]2[S:9][C:4]3[CH:3]=[C:2]([Br:1])[O:6][C:5]=3[CH:7]=2)[N:20]=[C:19]1[C@@H:36]1[CH2:40][CH2:39][CH2:38][N:37]1[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 583103862,5-Dibromo-thieno[3,2-b]furanHCID 672401812-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-5-tributylstannanyl-imidazole-1-carboxylic acid tert-butyl esterHCID 67240543(S)-2-{5-[5-(4-{2-[(S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-thieno[3,2-b]thiophen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 583104804-(2-bromo-thieno[3,2-b]furan-5-yl)-(S)-2-(1-tert-butoxycarbonyl-pyrrolidin-2-yl)-imidazole-1-carboxylic acid tert-butyl esterYield 16%

Procedure

Intermediate E81 was synthesized from 2,5-dibromo-thieno[3,2-b]furan (8.9 mmol) (Roowin) and intermediate 61 (9.35 mmol) following the procedure as described for the intermediate 63 (reaction time=6 hours and chromatography eluent: petroleum ether/AcOEt) to give intermediate E81 in 16% yield. MS (ESI, EI+) m/z=539 (MH+).

Workup

  1. customto give intermediate E81 in 16% yield

Sources & evidence

ORD record
ord-11c50e68175f41a59671a302067d9347
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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