Phenylboronic Acid → HCID 66958360, compound

HRID 1424687Notes

Reaction equation

HRID 1424687 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[CH:10])=[CH:5][CH:4]=1.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[N+:19]=[N-:20])=[CH:14][CH:13]=1.IN1CCOCC1.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:20]=[N:19][N:18]([C:15]3[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][CH:14]=3)[C:10]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 66827Phenylboronic AcidHCID 1374301-Azido-4-methylbenzeneHCID 2510201-Ethynyl-4-methoxybenzeneHCID 50918016HCID 50918016, compound

Product 1

HCID 66958360HCID 66958360, compound

Procedure

Synthesized from 4-methoxy-phenylacetylene, 4-methyl-phenylazide, N-iodomorpholine and phenylboronic acid using one-pot/three-step general procedure, 1.19 g, 3.50 mmol, 70%; mp=192-195° C. (dec.); IR (υ[cm−1]) 3019, 2937, 1619, 1517, 1481, 1370, 1247, 1177, 1027, 997, 842, 820, 747; 1H NMR (600 MHz, CDCl3) δ=7.50 (d, J=8.4, 2H), 7.39-7.30 (m, 3H), 7.20-7.11 (m, 6H), 6.83 (d, J=8.5, 2H), 3.78 (s, 3H), 2.34 (s, 3H); 13C NMR (151 MHz, CDCl3) δ=159.5, 144.8, 139.2, 134.3, 133.1, 130.4, 129.9, 129.4, 129.2, 128.8, 128.2, 125.2, 123.6, 114.1, 55.4, 21.4; HRMS (ESI-TOF) (m/z): [M+H]+ calcd for C22H20N3O, 342.1601; found 342.1605.

Sources & evidence

ORD record
ord-807518430e9f417a950535e07d26d2cb
Source dataset
uspto-grants-2015_01
Patent number
US08927736B2

Reaction notes

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