Reserpine → 2-(Boc-amino)-5-bromopyridine

HRID 251503Notes

Reaction equation

HRID 251503 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.BrC1C=CC(OC)=C(N[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])C=1.C(OCC)(=O)C.CCCCCCC.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)C2NC4C=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 5770ReserpineHCID 706222-Amino-5-bromopyridineHCID 17942658Tert-butyl (5-bromo-2-methoxyphenyl)carbamateHCID 21899848Ethylacetate heptane

Product 1

HCID 162178432-(Boc-amino)-5-bromopyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound was prepared from 5-bromo-2-pyridinamine in the manner described for compound (2): 1H NMR (DMSO-d6, 400 MHz) δ 9.96 (s, 1H), 8.49 (d, 1H), 7.93 (dd, 1H), 7.78 (d, 1H), 1.47 (s, 9H); TLC (ethyl acetate/heptane 5:95) Rf 0.28; RP-HPLC (Hypersil HyPurity Elite C18, 5 μm, 200 A, 250×4.6 mm; 25-100% acetonitrile-0.1 M ammonium acetate over 25 min, 1 ml/min) tr=18.50 min.

Sources & evidence

ORD record
ord-26f8ed8b7a324c9babdcf40b77d73d0b
Source dataset
uspto-grants-2011_01
Patent number
US07863444B2

Reaction notes

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