2-Amino-6-bromobenzonitrile → HCID 67401108, compound

HRID 711914Notes

Reaction equation

HRID 711914 reaction equation
CC1(C)C(C)(C)OB(/[CH:9]=[CH:10]/[CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)O1.[NH2:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26](Br)[C:23]=1[C:24]#[N:25]>>[NH2:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26](/[CH:9]=[CH:10]/[CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[C:23]=1[C:24]#[N:25]

Participants

3

Reactant 2

HCID 98130382-Amino-6-bromobenzonitrileHCID 10755307HCID 10755307, compound

Product 1

HCID 67401108HCID 67401108, compoundYield 47%

Procedure

Prepared as in Example 270a from (E)-4,4,5,5-tetramethyl-2-(4-(tetrahydro-2H-pyran-2-yloxy)but-1-enyl)-1,3,2-dioxaborolane (Example 273b) and 2-amino-6-bromobenzonitrile in 47% yield as a yellow gum. 1H NMR (400 MHz, CDCl3) δ 1.570 (m, 4H), 1.727 (m, 2H), 1.837 (m, 2H), 2.565 (q, J=6 Hz, 2H), 3.541 (m, 2H), 3.879 (m, 2H), 4.387 (br. s, 2H), 4.635 (m, 1H), 6.423 (d of t, J=7 Hz, 16 Hz, 1H), 6.586 (d, J=8 Hz, 1H), 6.710 (d, J=16 Hz, 1H), 6.905 (d, J=8 Hz, 1H), 7.237 (t, J=8 Hz, 1H).

Sources & evidence

ORD record
ord-d018d42fc08841dba5769bfe8fa6ea26
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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