Bromide ion → HCID 25254221, compound

HRID 219448Notes

Reaction equation

HRID 219448 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[C:13]([O:25][CH3:26])=[C:14]([C:22](=[O:24])[CH3:23])[C:15]([CH3:21])=[C:16]([CH3:20])[C:17]=2[O:18][CH3:19])=[CH:4][CH:3]=1.B(Cl)(Cl)Cl.Br[CH2:32][CH2:33]Br.[Br-].[NH:36]1[CH2:41]C[O:39][CH2:38][CH2:37]1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[C:13]([O:25][CH2:26][CH2:41][N:36]3[CH2:33][CH2:32][O:39][CH2:38][CH2:37]3)=[C:14]([C:22](=[O:24])[CH3:23])[C:15]([CH3:21])=[C:16]([CH3:20])[C:17]=2[O:18][CH3:19])=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 259Bromide ionHCID 78391,2-DibromoethaneHCID 8083MorpholineHCID 25135Boron TrichlorideHCID 59583524HCID 59583524, compound

Product 1

HCID 25254221HCID 25254221, compoundYield 33%

Procedure

Example 3b (50 mg, 0.139 mmol) was reacted with BCl3 (1.1 eq.) according to General Procedure C. The material thus obtained was then reacted with 1,2-dibromoethane (3.0 eq.) according to General Procedure F and the product bromide reacted with morpholine according to General Procedure G to afford the product as a clear oil (21 mg, 33% over 3 steps). 1H NMR (300 MHz, CDCl3) δ 7.19-7.14 (m, 2H), 6.98-6.93 (m, 2H), 4.09-4.00 (m, 4H), 3.77 (s, 3H), 3.71-3.68 (m, 4H), 2.79 (t, J=7.4 Hz, 2H), 2.62 (t, J=5.7 Hz, 2H), 2.50 (s, 3H), 2.49-2.46 (m, 4H), 2.11 (s, 3H), 2.05 (s, 3H), 2.05-1.97 (m, 2H).

Workup

  1. customThe material thus obtained

Sources & evidence

ORD record
ord-647885f05ca04a95ac9280bdb0f385e4
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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