Thiophene-3-boronic acid → HCID 131726976, compound

HRID 1909747Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:29]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30]1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[C:27]([C:31]3[CH:32]=[CH:33][S:29][CH:30]=3)=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 581760Thiophene-3-boronic acid

HCID 68997759HCID 68997759, compound

Product 1

HCID 131726976HCID 131726976, compoundYield 74%

Procedure

Followed the same procedure as that of step 1 in Example 107 with the use of (S)-2-[4-(4-iodo-benzyl)phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (2000 mg, 4 mmol), thiophene-3-boronic acid (1200 mg, 8 mmol) to afford the title product, (1300 mg, 74%); 1H NMR (400 MHz, CDCl3); δ 1.47 (s, 9H), 1.79-2.08 (m, 4H), 3.26-3.44 (m, 2H), 3.70-3.95 (m, 1H), 3.93 (s, 2H), 4.03-4.18 (m, 2H), 6.82-6.88 (m, 2H), 7.10 (d, J=8.0 Hz, 2H), 7.19 (d, J=8.0 Hz, 2H), 7.35-7.41 (m, 3H), 7.50 (d, J=8.0 Hz, 2H):

Sources & evidence

ORD record: ord-4f7ff65450b44d05bf34ab94a19870f5
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598359B2

Reaction notes

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