alpha-Bromo-o-fluorotoluene → (S)-1-(2-fluorobenzyl)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione

HRID 2191235Notes

Reaction equation

HRID 2191235 reaction equation
CN1C2C(=CC(S(N3CCC[C@H]3COC3C=CC=CC=3)(=O)=O)=CC=2)C(=O)C1=O.[O:29]([CH2:36][C@@H:37]1[CH2:40][CH2:39][N:38]1[S:41]([C:44]1[CH:45]=[C:46]2[C:50](=[CH:51][CH:52]=1)[NH:49][C:48](=[O:53])[C:47]2=[O:54])(=[O:43])=[O:42])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[F:55][C:56]1[CH:63]=[CH:62][CH:61]=[CH:60][C:57]=1[CH2:58]Br>>[F:55][C:56]1[CH:63]=[CH:62][CH:61]=[CH:60][C:57]=1[CH2:58][N:49]1[C:50]2[C:46](=[CH:45][C:44]([S:41]([N:38]3[CH2:39][CH2:40][C@H:37]3[CH2:36][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)(=[O:43])=[O:42])=[CH:52][CH:51]=2)[C:47](=[O:54])[C:48]1=[O:53]

Participants

4

Reactant 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 52888501-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneHCID 11624920(S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione

Product 1

HCID 11634372(S)-1-(2-fluorobenzyl)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione

Procedure

(S)-1-(2-Fluorobenzyl)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione (18f) was prepared according to the same procedure for compound 11a, except using compound 17 and 2-fluorobenzyl bromide, and purified with solid, mp 147.1-148.0° C. 1H NMR (300 MHz, CDCl3) δ 8.05 (d, J=1.8 Hz, 1H), 8.00 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.35 (m, 2H), 7.24-7.11 (m, 3H), 7.02-6.78 (m, 5H), 4.98 (s, 2H), 4.47 (m, 1H), 4.11 (m, 2H), 3.85 (m, 2H), 2.35-2.25 (m, 2H). Anal. Calcd for C25H21FN2O5S: C, 62.49, H, 4.41; N, 5.83. Found: C, 62.25, H, 4.47; N, 5.68.

Workup

  1. custompurified with solid, mp 147.1-148.0° C

Sources & evidence

ORD record
ord-94a5c7114bd5467aa5418a2adcec434a
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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