6-Bromopyridine-2-carbaldehyde → 4-[(6-Bromopyridin-2-yl)methyl]thiomorpholine 1,1-dioxide

HRID 2060599Notes

Reaction equation

HRID 2060599 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:10]2[CH2:15][CH2:14][S:13](=[O:17])(=[O:16])[CH2:12][CH2:11]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 27570096-Bromopyridine-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 6484228Thiomorpholine 1,1-dioxide

Product 1

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

Procedure

The title compound was prepared as described in Example 2, Step 1 using 6-bromopyridine-2-carbaldehyde (3.0 g, 16.13 mmol), thiomorpholine 1,1-dioxide (2.18 g, 16.13 mmol), and sodium triacetoxyborohydride (4.79 g, 22.58 mmol) as starting materials. 1H NMR (600 MHz, d6-DMSO) δ 7.72 (t, 1H), 7.51 (d, 1H), 7.50 (d, 1H), 3.74 (s, 2H), 3.10 (m, 4H), 2.90 (m, 4H).

Sources & evidence

ORD record
ord-e6ac2623d6a4454f8c8742cd484d2790
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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