2,2,2-Trifluoro-1-(7-iodo-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl)ethanone → 2,2,2-Trifluoro-1-(7-(oct-1-ynyl)-1,2,4,5-tetrahydrobenzo-[d]azepin-3-yl)ethanone

HRID 710488Notes

Reaction equation

HRID 710488 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13](I)[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].I[C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH2:25]N(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:23]2>>[F:1][C:2]([F:18])([F:17])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([C:23]#[C:22][CH2:21][CH2:20][CH2:28][CH2:27][CH2:26][CH3:25])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 189436202,2,2-Trifluoro-1-(7-iodo-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl)ethanoneHCID 667262485-Iodo-2-tritylisoindoline

Product 1

HCID 866618182,2,2-Trifluoro-1-(7-(oct-1-ynyl)-1,2,4,5-tetrahydrobenzo-[d]azepin-3-yl)ethanoneYield 73%

Procedure

When the product of Step B was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 73% yield, as a pale oil. 1H-NMR (CDCl3) 0.9 (tr, 3H), 1.28-1.33 (m, 10H); 1.42-1.46 (m, 2H); 2.88-2.96 (m, 4H); 3.64-3.67 (m, 2H); 3.71-3.75 (m, 2H); 7.05 (tr, 1H, J=7.92 Hz), 7.13-7.2 (m, 2H).

Sources & evidence

ORD record
ord-f3f53f7c8d5942f58b21992f9753daed
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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