1H-Benzotriazole-1-methanol → 2-(6-Bromopyridin-2-yl)-2-(1,1-dioxidothiomorpholin-4-yl)ethanol

HRID 2060600Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]2)[CH:5]=[CH:4][CH:3]=1.N1([CH2:26][OH:27])C2C=CC=CC=2N=N1.[Li+].CC([N-]C(C)C)C>>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([N:9]2[CH2:10][CH2:11][S:12](=[O:15])(=[O:16])[CH2:13][CH2:14]2)[CH2:26][OH:27])[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 2241691H-Benzotriazole-1-methanol

HCID 2724682Lithium diisopropylamide

HCID 583352584-[(6-Bromopyridin-2-yl)methyl]thiomorpholine 1,1-dioxide

Product 1

HCID 583352772-(6-Bromopyridin-2-yl)-2-(1,1-dioxidothiomorpholin-4-yl)ethanol

Procedure

The title compound was prepared as described in Example 3, Step 1 using 4-[(6-bromopyridin-2-yl)methyl]thiomorpholine 1,1-dioxide (2.94 g, 9.63 mmol), 1H-1,2,3-benzotriazol-1-ylmethanol (2.87, 19.17 mmol), and LDA (16 mL of 1.8 M in tetrahydrofuran/heptane/ethylbenzene) as starting materials. LRMS (APCI) calcd for C11H16BrN2O3S [M+H]+: 335.0, Found: 334.9.

Sources & evidence

ORD record: ord-09984169836f4135b9e85f647d5346a7
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278335B2

Reaction notes

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