Bromine → HCID 54279563, compound

HRID 1873164Notes

Reaction equation

HRID 1873164 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[C:11]3[C:16]([C:17]([C:27]#[N:28])=[C:18]4[S:22][C:21]5[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=5[C:19]=24)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].O[C@H:30]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:31]([O:33]C)=[O:32].BrBr>>[Br:9][C:6]1[CH:5]=[C:4]([C:10]2[C:19]3[C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[S:22][C:18]=3[C:17]([C:27]#[N:28])=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[CH:15]3)[CH:3]=[C:2]([Br:1])[C:7]=1[O:8][C@@H:30]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:31]([OH:33])=[O:32]

Participants

4

Reactant 3

HCID 24408BromineHCID 10986876methyl (2R)-2-hydroxy-3-phenylpropanoateHCID 18687858HCID 18687858, compound

Product 1

HCID 54279563HCID 54279563, compound

Procedure

Prepared from 11-(3, 5-dibromo-4-hydroxy-phenyl)-benzo[b]naphtho[2,3-d ]thiophene-6-carbonitrile (Example 58) and (R)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 97). White solid: mp 176-178° C.: NMR (CDCl3); δ8.36 (ddd, J =8,1,1 Hz, 1 H), 7.85 (d, J=8 Hz, 1 H), 7.77 (ddd, J=8, 8, 2 Hz, 1 H), 7.58 (d, J=2 Hz, 1 H), 7.61-7.54 (m, 2 H), 7.56 (d, J=2 Hz, 1 H), 7.47 (ddd, J=8, 8, 1 Hz, 1 H), 7.41 (ddd, J=8, 1, 1, 2 H ), 7.36-7.26 (m, 3 H), 7.20 (ddd, J=8, 8, 1, 1 H), 6.75 (ddd, J =8, 1, 1 Hz, 1 H), 5.46 (t, J=7 Hz, 1 H), 3.59 (d, J=7 Hz, 2 H); MS (-FAB): [M-H]-, 2 bromine isotope pattern, 654 (2%), 656 (4%) 658 (2%); Anal. Calc. for C32H19Br2NO3S: C, 58.47, H, 2.91, N, 2.13 Found: C, 58.23, H, 2.69, N, 2.03.

Sources & evidence

ORD record
ord-3b996117e2004810937175963e090b7c
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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