Ammonia → HCID 57110447, compound

HRID 1417539Notes

Reaction equation

HRID 1417539 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12])[C:5]#[N:6].[F:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[C@@H:33]([CH2:34][OH:35])[CH2:32][CH2:31][C@:22]32[O:26][CH2:25][C:24]([Sn](C)(C)C)=[CH:23]3)=[CH:17][CH:16]=1.N>>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[C@@H:33]([CH2:34][OH:35])[CH2:32][CH2:31][C@@:22]32[O:26][CH2:25][C:24]([C:2]2[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=2[O:10][CH:11]([CH3:13])[CH3:12])=[CH:23]3)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 54336731HCID 54336731, compoundHCID 86753766HCID 86753766, compound

Product 1

HCID 57110447HCID 57110447, compound

Procedure

The title compound was prepared following the procedure described in Example 6, Step F(d) using 3-bromo-4-isopropoxybenzonitrile and (5R,6S,7S)-6-(4-fluorophenyl)-3-(trimethylstannyl)-1-oxaspiro[4.4]non-3-ene-7-methanol as substrates for the cross-coupling reaction. 400 MHz 1H NMR (CD3OD): δ 1.28 (s, 3H), 1.31 (s, 3H), 1.70 (m, 1H), 2.18 (m, 2H), 2.72 (m, 1H), 2.82 (d, 1H), 3.37 (dd, 1H), 3.55 (dd, 1H), 4.05 (dd, 1H), 4.67 (dd, 1H), 4.70 (m, 1H), 6.35 (m, 1H), 6.92 (t, 2H), 7.07 (d, 1H), 7.30 (m, 2H), 7.38 (d, 1H), 7.52 (dd, 1H); Mass spec (NH3 /CI): 408 (M+1); 425 (M+NH3).

Workup

  1. customfor the cross-coupling reaction

Sources & evidence

ORD record
ord-9359ca5fe2134db18e42c2f1dc053e0b
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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