Tetrahydro-4H-pyran-4-ol → 2-amino-6-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile

HRID 2169973Notes

Reaction equation

HRID 2169973 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[NH2:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13](F)[C:10]=1[C:11]#[N:12]>>[NH2:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([O:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[C:10]=1[C:11]#[N:12]

Participants

3

Reactant 2

HCID 74956Tetrahydro-4H-pyran-4-olHCID 5226592-Amino-6-fluorobenzonitrile

Product 1

HCID 667459382-amino-6-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile

Procedure

Prepared as in Example 22b from tetrahydro-2H-pyran-4-ol and 2-amino-6-fluorobenzonitrile as a colorless oil (48%). 1H NR (400 MHz, CDCl3) δ 1.87 (m, 2H), 2.00 (m, 2H), 3.63 (m, 2H), 4.00 (m, 2H), 4.42 (s, 2H), 4.58 (m, 1H), 6.23 (d, J=8.4 Hz, 1H), 6.30 (d, J=8.4 Hz, 1H), 7.20 (t, J=8.4 Hz, 1H). MS 219 (MH+).

Sources & evidence

ORD record
ord-02fc9319c6284f429c87766bcfadf8fd
Source dataset
uspto-grants-2015_06
Patent number
US09049878B2

Reaction notes

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