2-Amino-6-bromobenzonitrile → HCID 67400820, compound

Reaction equation

[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:6][C@H:5]1B(O)O.[NH2:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[C:12]=1[C:13]#[N:14]>>[NH2:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([C@@H:5]2[CH2:6][C@H:4]2[CH2:3][O:2][CH3:1])[C:12]=1[C:13]#[N:14]

Participants

Reactant 2

HCID 98130382-Amino-6-bromobenzonitrile

HCID 57416267[(1R,2R)-2-(Methoxymethyl)cyclopropyl]boronic acid

Product 1

HCID 67400820HCID 67400820, compoundYield 64%

Procedure

Prepared as in Example 270a from (±)-trans-2-(methoxymethyl)cyclopropylboronic acid (example 271b) and 2-amino-6-bromobenzonitrile in 64% yield as a yellowish brown waxy solid. 1H NMR (400 MHz, DMSO-d6) δ 0.932 (m, 2H), 1.341 (m, 1H), 1.879 (m, 1H), 2.324 (s, 3H), 3.351 (d, J=6 Hz, 2H), 5.896 (br. s, 2H), 6.148 (d, J=8 Hz, 1H), 6.550 (d, J=8 Hz, 1H), 7.130 (t, J=8 Hz, 1H).

Sources & evidence

ORD record: ord-abc608da42e645fca79b155136c54d2e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181276B2

Reaction notes

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