2,5-Dibromopyridine → HCID 13979741, compound

HRID 1182496Notes

Reaction equation

HRID 1182496 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.BrC1C=CC(C(CCCCCCC(OCC)=O)=O)=CC=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:36]=1[O:37][CH3:38].S1C=CC(B(O)O)=C1>>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)[CH:34]=[CH:35][C:36]=1[O:37][CH3:38]

Participants

5

Reactant 4

HCID 693532,5-DibromopyridineHCID 581760Thiophene-3-boronic acidHCID 27347023,4-Dimethoxyphenylboronic acidHCID 11024292ETHYL 8-(4-BROMOPHENYL)-8-OXOOCTANOATE

Product 1

HCID 13979741HCID 13979741, compoundYield 78%

Procedure

Following the procedure described in Example 67, step 1, but substituting respectively 2,5-dibromopyridine for 49d and 3,4-dimethoxyphenyl boronic acid for 3-thiophene boronic acid, the title compound 147 was obtained in 78% Yield. 1H NMR (300 MHz, CDCl3): δ 8.65 (dd, J=2.4, 0.9 Hz, 1H), 7.77 (dd, J=8.4, 5.4 Hz, 1H), 7.60 (d, J=2.1 Hz, 1H), 7.53 (dd, J=8.4, 0.9 Hz, 1H), 7.73 (dd, J=8.4, 2.1 Hz, 1H), 6.89 (d, J=8.4 Hz, 1H), 3.95 (s, 3H), 3.90 (s, 3H). 13C NMR (75 MHz, CDCl3): δ 55.92, 55.93, 109.64, 111.01, 118.46, 119.25, 120.92, 131.05, 139.09, 149.28, 150.21, 150.3 6, 155.40.

Sources & evidence

ORD record
ord-68a9a9d863344b34abf1f219897142bb
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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