Sodium Azide → HCID 86596995, compound

HRID 494731Notes

Reaction equation

HRID 494731 reaction equation
ClC1C(C(O)=O)=CN=C(Cl)C=1C.BrC1C=CC(NC2C(C(O)=O)=CN3C=CN=C3C=2C)=C(Cl)C=1.[N-:35]=[N+:36]=[N-:37].[Na+].[CH3:39][O:40][C:41](=[O:59])[C:42]1[C:47]([NH:48][C:49]2[CH:54]=[CH:53][C:52]([Br:55])=[CH:51][C:50]=2[Cl:56])=[C:46]([CH3:57])[C:45](Cl)=[N:44][CH:43]=1>>[CH3:39][O:40][C:41](=[O:59])[C:42]1[C:47]([NH:48][C:49]2[CH:54]=[CH:53][C:52]([Br:55])=[CH:51][C:50]=2[Cl:56])=[C:46]([CH3:57])[C:45]([N:35]=[N+:36]=[N-:37])=[N:44][CH:43]=1

Participants

5

Reactant 4

HCID 33557Sodium AzideHCID 107269464,6-dichloro-5-methylnicotinic acidHCID 21111553HCID 21111553, compoundHCID 58886666HCID 58886666, compound

Product 1

HCID 86596995HCID 86596995, compound

Conditions

Temperature
50 °C

Procedure

4,6-Dichloro-5-methylnicotinic acid (J. Heterocyclic Chemistry 1999, 36, 953-957) was converted to 7-(4-bromo-2-chloro-phenylamino)-8-methylimidazo[1,2-a]pyridine-6-carboxylic acid according to the steps described in the alternate synthesis of Step D, Example 9. It was determined that addition of sodium azide to the 4-(4-bromo-2-chloro-phenylamino)-6-chloro-5-methylnicotinic acid methyl ester intermediate required heating to 50° C., which results in a separable mixture of the desired methyl ester, 6-azido-4-(4-bromo-2-chlorophenylamino)-5-methylnicotinic acid methyl ester, and the corresponding carboxylic acid. MS ESI (+) m/z 380, 382 (M+, Cl, Br pattern) detected. 1H NMR (400 MHz, DMSO-d6) δ 9.46 (s, 1H), 9.40 (br s, 1H), 8.25 (d, 1H), 8.12 (d, 1H), 7.79 (m, 1H), 7.42 (dd, 1H), 6.80 (d, 1H), 2.07 (s, 3H).

Workup

  1. customdescribed in the alternate synthesis of Step D, Example 9

Sources & evidence

ORD record
ord-c236ef8ea6804f92a3383290ebe900a9
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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